Lindsay Lohan, Winona Ryder and Robert Downey Jr. have more than a criminal record in common.  All three actors also suffered the loss of movie roles due to their criminal convictions. 
Woody Allen, who was forced to jettison both Robert Downey Jr. and Winona Ryder from one of his movie projects, Melinda and Melinda, told biographer Eric Lax that he was desperate to cast Downey and Ryder but that “[they] could not get insurance on them . . . We couldn’t get bonded. The completion bonding companies would not bond the picture unless we could insure them.”

At the time, Downey was recovering from years of drug addiction, which included several arrests and jail time, and  Ryder was on probation from her 2001 conviction of felony grand theft for shoplifting.   Lohan was similarly dropped from a Shirley MacLaine project following a 2007 arrest for suspicion of driving under the influence and with a suspended license. 
"It’s Lohan’s criminal record that may keep her out of work", says Wendy Diaz, an executive at Fireman’s Fund, one of the largest film insurance companies in Hollywood. “We cover cast members who get sick, injured, or die. If an actor is incarcerated, that isn’t covered, so the studio loses money and cannot reclaim it.”  Even if producers are successful in obtaining insurance on actors in trouble with the law, they may entertain second thoughts about employing them because insurers will simply exclude coverage where necessary.  Moreover, producers may fear a relapse.